2-formyl-9,10-bis(dicyanomethylene)anthracene | 189040-55-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-formyl-9,10-bis(dicyanomethylene)anthracene
• 英文别名: 2,2'-(2-Formylanthracene-9,10-diylidene)dipropanedinitrile；2-[10-(dicyanomethylidene)-3-formylanthracen-9-ylidene]propanedinitrile
• CAS: 189040-55-9
• 化学式: C₂₁H₈N₄O
• 分子量: 332.321
• InChiKey: ZKOHOAFVOWDINN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-formyl-9,10-bis(dicyanomethylene)anthracene 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以52%的产率得到2-formyl-9,10-bis(dicyanomethylene)anthraquinone oxime
  参考文献：
  名称：

  [60]Fullerene Adducts with Improved Electron Acceptor Properties

  摘要：

  The synthesis of C-60-based dyads in which the C-60 core is covalently attached to a strong electron acceptor moiety such as quinones, TCNQ or DCNQI derivatives, has been carried out by 1,3-dipolar cycloaddition of "in situ" generated azomethyne ylides or nitrile oxides to C-60. As expected, the obtained pyrrolidino[3',4':1,2][60]fullerenes exhibit reduction potentials of the C-60 framework which are cathodically shifted in comparison with the parent C-60. In contrast, isoxazolo[4',5':1,2][60]fullerenes show reduction waves for the fullerene core that are anodically shifted in comparison with the parent C-60, which indicates that they are remarkably stronger accepters than C-60. The electron acceptor organic addend also undergoes an anodic shift due to the electronic interaction with the C-60 moiety. The molecular geometry of pyrrolidinofullerenes has been calculated at the semiempirical PM3 level and reveals a highly distorted geometry for the acceptor moiety in compound 13, and a most stable conformation in which both dicyanomethylene units are far away from the C-60 surface.

  DOI：

  10.1021/jo0003753
• 作为产物：
  描述：

  2-羟甲基蒽醌 在 吡啶 、 四氯化钛 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-formyl-9,10-bis(dicyanomethylene)anthracene
  参考文献：
  名称：

  [60]Fullerene Adducts with Improved Electron Acceptor Properties

  摘要：

  The synthesis of C-60-based dyads in which the C-60 core is covalently attached to a strong electron acceptor moiety such as quinones, TCNQ or DCNQI derivatives, has been carried out by 1,3-dipolar cycloaddition of "in situ" generated azomethyne ylides or nitrile oxides to C-60. As expected, the obtained pyrrolidino[3',4':1,2][60]fullerenes exhibit reduction potentials of the C-60 framework which are cathodically shifted in comparison with the parent C-60. In contrast, isoxazolo[4',5':1,2][60]fullerenes show reduction waves for the fullerene core that are anodically shifted in comparison with the parent C-60, which indicates that they are remarkably stronger accepters than C-60. The electron acceptor organic addend also undergoes an anodic shift due to the electronic interaction with the C-60 moiety. The molecular geometry of pyrrolidinofullerenes has been calculated at the semiempirical PM3 level and reveals a highly distorted geometry for the acceptor moiety in compound 13, and a most stable conformation in which both dicyanomethylene units are far away from the C-60 surface.

  DOI：

  10.1021/jo0003753

文献信息

• New Chiral Binaphthyl Building Blocks:  Synthesis of the First Optically Active Tetrathiafulvalene and 11,11,12,12-Tetracyano-9,10-anthraquinodimethane Dimers
  作者：Rafael Gómez、José L. Segura、Nazario Martín

  DOI：10.1021/jo0009649

  日期：2000.11.1

  rotation of the two naphthalene rings, binaphthyl derivatives are ideal candidates to be used as nonplanar spacers between electroactive units in the search for materials with enhanced dimensionality. The electronic absorption spectra of dimers in which the electroactive unit is in conjugation with the naphthalene fragment reveal the presence of intramolecular photoinduced electron-transfer process from

  已经合成了带有三苯基膦或膦酸酯基团的新对映体纯的联萘衍生物，并将其用作制备第一个光学活性TTF和TCAQ二聚体的基础材料。由于两个萘环的旋转受限制，联萘衍生物是寻找具有增强尺寸的材料时理想的候选物，可用作电活性单元之间的非平面间隔基。电活性单元与萘片段共轭的二聚体的电子吸收光谱揭示了分子内光致电子转移过程的存在，该过程是在5和6中从TTF到萘单元，以及在7中从萘部分到TCAQ单元。 。
• A Fully Conjugated TTF-π-TCAQ System: Synthesis, Structure, and Electronic Properties
  作者：José Santos、Beatriz M. Illescas、Nazario Martín、Javier Adrio、Juan C. Carretero、Rafael Viruela、Enrique Ortí、Fabian Spänig、Dirk M. Guldi

  DOI：10.1002/chem.201002674

  日期：2011.3.1

  sulfonylmethyl‐exTTFs (exTTF=2‐[9‐(1,3‐dithiol‐2‐ylidene)anthracen‐10(9H)‐ylidene]‐1,3‐dithiole)—prepared as new building blocks—were linked. A variety of experimental conditions reveal that the use of sodium hexamethyldisilazane (NaHMDS) as base in THF afforded the E olefins with excellent stereoselectivity. Theoretical calculations at the B3LYP/6‐31G** level point to highly distorted exTTF and TCAQ that

  第一个完全共轭的四硫富瓦烯-四氰基-对-喹二甲烷（（TTF）-TCNQ）型系统的合成是通过Julia-Kocienski烯烃化反应进行的。特别是四氰基蒽醌二甲烷（TCAQ）甲酰基衍生物和两个新的磺酰基甲基-exTTF（exTTF = 2- [9-（9，（1,3-二硫醇-2-亚烷基））蒽-10（9 H）-亚烷基] -1,3-已被链接为二硫醇（准备作为新的构建基块）。各种实验条件表明，使用六甲基二硅氮烷钠（NaHMDS）作为THF中的碱可提供E具有优异的立体选择性的烯烃。在B3LYP / 6-31G **水平上的理论计算表明，高度扭曲的exTTF和TCAQ在它们之间形成了几乎平面的二苯乙烯单元。尽管计算预测了供体和受体之间可观的电子通讯，但循环伏安法研究并未证实这种作用。只是在光物理测定中，电子通信才以电荷转移（CT）吸收和发射的形式出现。一旦被光激发（即局部激发态或激发的电荷转移态），亚皮秒
• Photoinduced Charge Transfer between Tetracyano-Anthraquino-Dimethane Derivatives and Conjugated Polymers for Photovoltaics
  作者：Gerald Zerza、Markus C. Scharber、Christroph J. Brabec、N. Serdar Sariciftci、Rafael Gómez、José L. Segura、Nazario Martín、Vojislav I. Srdanov

  DOI：10.1021/jp000729u

  日期：2000.9.1

  The photoinduced charge transfer between tetracyano-anthraquino-dimethane (TCAQ) derivatives and poly[2-methoxy-5-(3,7-dimethyloctyloxy)-1,4-phenylenevinylene] (MDMO−PPV) has been studied by photoinduced absorption (PIA) spectroscopy in the VIS and IR spectral region and by light induced electron spin resonance (LESR). Studies on three different TCAQ derivatives with different side chain substitutions

  通过光诱导吸收 (PIA) 研究了四氰基蒽醌二甲烷 (TCAQ) 衍生物与聚[2-甲氧基-5-(3,7-二甲基辛氧基)-1,4-亚苯基亚乙烯基] (MDMO-PPV) 之间的光诱导电荷转移。 ) 在 VIS 和 IR 光谱区域中的光谱和光诱导电子自旋共振 (LESR)。报道了对具有不同侧链取代的三种不同 TCAQ 衍生物的研究。其中，已合成了一种与富勒烯相连的 TCAQ 超分子，用作串联电子受体。在可见光/近红外范围内的光致吸收显示出一个大约 1.8 eV 的宽平台，然后是 1.35 和 1.24 eV 的两个峰，对于与 MDMO-PPV 复合的所有三个受体，还有一个低于 0.5 eV 的额外宽特征。所有 PIA 特征都具有幂律激发强度依赖性，其指数接近 0.5，正如双分子动力学所预期的那样。LESR 研究表明，g 因子为 2.0028，宽度（峰到峰）为 3.5 G，源自 TCAQ ...
• [60]Fullerene-based electron acceptors with tetracyano-p-quinodimethane (TCNQ) and dicyano-p-quinonediimine (DCNQI) derivatives
  作者：Beatriz Illescas、Nazario Martín、Carlos Seoane

  DOI：10.1016/s0040-4039(97)00220-7

  日期：1997.3

  The first TCNQ and DCNQl derivatives of [60]fullerene are reported. Cyclic voltammetry indicates that the attachment of the first electron in the reduction process takes place in the organic addend. (C) 1997 Elsevier Science Ltd.
• An Endohedral Metallofullerene as a Pure Electron Donor: Intramolecular Electron Transfer in Donor–Acceptor Conjugates of La₂@C₈₀ and 11,11,12,12-Tetracyano-9,10-anthra-<i>p</i>-quinodimethane (TCAQ)
  作者：Yuta Takano、Shota Obuchi、Naomi Mizorogi、Raúl García、M. Ángeles Herranz、Marc Rudolf、Dirk M. Guldi、Nazario Martín、Shigeru Nagase、Takeshi Akasaka

  DOI：10.1021/ja307341g

  日期：2012.11.28

  An endohedral metallofullerene, La-2@C-80, is covalently linked to the strong electron acceptor 11,11,12,12-tetracyano-9,10-antha-p- quinodimethane (TCAQ) by means of the Prato reaction, affording two different [5,6]-metallofulleropyrrolidines namely 1a and 2a, 1a and 2a were isolated and fully characterized by means of MALDI-TOF mass, UV-Vis-NIR absorption and NMR spectroscopies. In addition, cyclic voltammetry (CV) and differential pulse voltammetry (DPV) corroborated the unique redox character of 2a, that is the presence of the electron donating La-2@C-80 and the electron accepting TCAQ, Although a weak electronic coupling 'dictates the interactions between La-2@C-80 and TCAQ in the ground state, time resolved transient absorption experiments reveal that in the excited (i.e., pi-pi* centered at La-2@C-80) the unprecedented formation of the (La-2@C-80)(center dot+)-(TCAQ)(center dot-) radical ion pair state eevolves in nonpolar and polar media with a quantum efficiency of 33%.